Andy Molinsky: I have struggled, just like everybody, in stepping outside my comfort zone. So in Reach I talk about that. I interviewed and observed managers and leaders, [including] doctors (pediatric physicians in particular). I went out with two officers in a squad car for an entire day, in a pretty tough part of a major metropolitan city. I had the bulletproof vest on and everything. [I also interviewed] actors, students, priests, rabbis, teachers, even a goat farmer. I really tried to take a wide lens on this issue to understand people who find ways to stretch outside their comfort zone.

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I found five psychological challenges, core ones that kept occurring. The first is authenticity, the idea that when I'm stepping outside my comfort zone and acting in a way that is new and different for me, I just don't feel like who I normally feel like.

Another one I found is what I call the likability challenge: the worry that people won't like this version of me if I act in this way.

The third one is competence: the worry that we won't be good at this, and that others will see that we're not good at this.

Resentment is the fourth one: feeling resentful and angry, frustrated that you have to do this in the first place. A lot of introverts tell me this. “Why do I have to make small talk and chit chat? Why do I have to network?

The last one is morality. And this doesn't happen in all cases. But morality would be the idea that what I need to do when stepping outside my comfort zone feels wrong. I open the book with a story of a young woman, an entrepreneur, who had to fire her best friend from her startup.

There are a lot of potential pain points here, and often people experience more than one.

Arruda: What are the things that we can do to alleviate some of those psychological barriers?

Molinsky: I found three key things. The first is what I would call conviction, having that deep sense of purpose in the reason that you're doing this. Having that wind at your back.

The second key I found was customization—the extent to which people were able to make minor tweaks or adjustments to the situations they found themselves in, to make it just that little bit easier to do. Some people did it through body language. Other people used props, a lucky charm. Other people can influence the context, so bring a friend to the networking event, put buddies in the audience if you're giving a speech, or before the speech go talk to a few people to feel more comfortable.

The last one is clarity. Fear and anxiety can really take hold of us and make us go to extremes. “I have to give this pubic speech. I'm going to be awful at it. I'll be a complete failure.” When you're stepping outside your comfort zone, try to anchor yourself in the middle ground to try to have a more normalized, reasonable perspective. People who are able to find a way of developing clarity in their situation were more successful.

Arruda: What are some of the benefits and costs of avoiding stepping outside your comfort zone?

Molinsky: The big benefit of avoidance is relief. But you're just delaying the inevitable and also increasing the difficulty of ultimately doing it. So that's the catch with avoidance. It's very seductive, but at the same time it makes it harder the next time around. It’s really critical to have a mindset that focuses on learning as opposed to mere performance.

Try to find something that's at the intersection between potentially doable and high impact—something that's going to really add some value to your life and that's going to ideally give you a quick, small win.

Arruda: Let's talk about when you step outside your comfort zone, and it doesn't necessarily work.

Molinsky: That's really hard. Preparation would be one thing, in terms of increasing the chances of success. I think it's critical in those situations to come back to the three C's, especially conviction. How important is this development? How important is this role? If it's really, really important, my hope would be that it would be a source of motivation and inspiration to step back into another opportunity. It should be a “just right” type of situation.

Arruda: What have you personally learned about taking steps outside your comfort zone?

Molinsky: I was the kid in college who never spoke in class. Never. I would sit in the back. I would consider raising my hand, but my heart would beat like it's like jumping out of my chest. Now I enjoy public speaking, twenty years later. You know what the biggest thing has been? Social media. I had this naïve idea that you write a book and press “send” on the computer and everyone goes and buys it. That doesn't happen. It requires social media. It requires putting yourself out there. To this day, I get queasy whenever I press “send” on a tweet or a post that has a whiff of self-promotion to it. But I do it [because] I have this sense of conviction that I can really impact people's lives.